Banoxantrone| AQ4N | CAS#136470-65-0

MedKoo Cat#: 200430 | Name: Banoxantrone (AQ4N)

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Banoxantrone is a bioreductive, alkylaminoanthraquinone prodrug with antineoplastic activity. Under hypoxic conditions, often seen in solid tumors, banoxantrone (AQ4N) is converted and activated by cytochrome P450 enzymes, which are upregulated in certain tumors, to the cytotoxic DNA-binding agent AQ4. Banoxantrone intercalates into and crosslinks DNA, and inhibits topoisomerase II. This results in an inhibition of DNA replication and repair in tumor cells. Combined with conventional therapeutic agents, both oxygenic and hypoxic regions of tumors can be targeted.

Chemical Structure

Banoxantrone (AQ4N)

CAS#136470-65-0 (free)

Theoretical Analysis

MedKoo Cat#: 200430

Name: Banoxantrone (AQ4N)

CAS#: 136470-65-0 (free)

Chemical Formula: C22H28N4O6

Exact Mass: 444.2009

Molecular Weight: 444.48

Elemental Analysis: C, 59.45; H, 6.35; N, 12.60; O, 21.60

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

136470-65-0 (free) 252979-56-9 (HCl)

Synonym

AQ-4N; AZD-1689; AQ4N; AZD1689; AQ 4N; AZD 1689

IUPAC/Chemical Name

2,2'-(5,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-1,4-diyl)bis(azanediyl)bis(N,N-dimethylethanamine oxide)

InChi Key

YZBAXVICWUUHGG-UHFFFAOYSA-N

InChi Code

InChI=1S/C22H28N4O6/c1-25(2,31)11-9-23-13-5-6-14(24-10-12-26(3,4)32)18-17(13)21(29)19-15(27)7-8-16(28)20(19)22(18)30/h5-8,23-24,27-28H,9-12H2,1-4H3

SMILES Code

O=C(C1=C2C(O)=CC=C1O)C3=C(NCC[N+](C)([O-])C)C=CC(NCC[N+](C)([O-])C)=C3C2=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>5 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 444.48 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Gieling RG, Fitzmaurice RJ, Telfer BA, Babur M, Williams KJ. Dissemination via the lymphatic or angiogenic route impacts the pathology, microenvironment and hypoxia-related drug response of lung metastases. Clin Exp Metastasis. 2015 Jun 26. [Epub ahead of print] PubMed PMID: 26112891. 2: Guise CP, Mowday AM, Ashoorzadeh A, Yuan R, Lin WH, Wu DH, Smaill JB, Patterson AV, Ding K. Bioreductive prodrugs as cancer therapeutics: targeting tumor hypoxia. Chin J Cancer. 2014 Feb;33(2):80-6. doi: 10.5732/cjc.012.10285. Epub 2013 Jul 12. Review. PubMed PMID: 23845143; PubMed Central PMCID: PMC3935009. 3: Manley E Jr, Waxman DJ. Impact of tumor blood flow modulation on tumor sensitivity to the bioreductive drug banoxantrone. J Pharmacol Exp Ther. 2013 Feb;344(2):368-77. doi: 10.1124/jpet.112.200089. Epub 2012 Nov 28. PubMed PMID: 23192656; PubMed Central PMCID: PMC3558827. 4: Ming L, Byrne NM, Camac SN, Mitchell CA, Ward C, Waugh DJ, McKeown SR, Worthington J. Androgen deprivation results in time-dependent hypoxia in LNCaP prostate tumours: informed scheduling of the bioreductive drug AQ4N improves treatment response. Int J Cancer. 2013 Mar 15;132(6):1323-32. doi: 10.1002/ijc.27796. Epub 2012 Nov 23. PubMed PMID: 22915157. 5: Bebenek IG, Solaimani P, Bui P, Hankinson O. CYP2S1 is negatively regulated by corticosteroids in human cell lines. Toxicol Lett. 2012 Feb 25;209(1):30-4. doi: 10.1016/j.toxlet.2011.11.020. Epub 2011 Nov 30. PubMed PMID: 22155357. 6: Xiao Y, Shinkyo R, Guengerich FP. Cytochrome P450 2S1 is reduced by NADPH-cytochrome P450 reductase. Drug Metab Dispos. 2011 Jun;39(6):944-6. doi: 10.1124/dmd.111.039321. Epub 2011 Mar 23. PubMed PMID: 21430234; PubMed Central PMCID: PMC3100906. 7: Nishida CR, Lee M, de Montellano PR. Efficient hypoxic activation of the anticancer agent AQ4N by CYP2S1 and CYP2W1. Mol Pharmacol. 2010 Sep;78(3):497-502. doi: 10.1124/mol.110.065045. Epub 2010 Jun 21. PubMed PMID: 20566689; PubMed Central PMCID: PMC2939484. 8: Williams KJ, Albertella MR, Fitzpatrick B, Loadman PM, Shnyder SD, Chinje EC, Telfer BA, Dunk CR, Harris PA, Stratford IJ. In vivo activation of the hypoxia-targeted cytotoxin AQ4N in human tumor xenografts. Mol Cancer Ther. 2009 Dec;8(12):3266-75. doi: 10.1158/1535-7163.MCT-09-0396. Epub . PubMed PMID: 19996276. 9: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2009 Apr;31(3):183-226. PubMed PMID: 19536362. 10: Mehibel M, Singh S, Chinje EC, Cowen RL, Stratford IJ. Effects of cytokine-induced macrophages on the response of tumor cells to banoxantrone (AQ4N). Mol Cancer Ther. 2009 May;8(5):1261-9. doi: 10.1158/1535-7163.MCT-08-0927. Epub 2009 May 12. PubMed PMID: 19435866.